EP0711781A1 - Organosilicon compound and a method for preparing the same - Google Patents
Organosilicon compound and a method for preparing the same Download PDFInfo
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- EP0711781A1 EP0711781A1 EP95308053A EP95308053A EP0711781A1 EP 0711781 A1 EP0711781 A1 EP 0711781A1 EP 95308053 A EP95308053 A EP 95308053A EP 95308053 A EP95308053 A EP 95308053A EP 0711781 A1 EP0711781 A1 EP 0711781A1
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- organosilicon compound
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- monovalent hydrocarbon
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/21—Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
Definitions
- the present invention relates to an organosilicon compound useful as a crosslinking agent for addition-reaction curable silicone rubber compositions for use in various uses, and to a method for preparing the organosilicon compound.
- an addition-reaction curable silicone rubber composition comprising an organopolysiloxane having, as a base polymer, an alkenyl group such as vinyl group and, as a crosslinking agent, an organohydrogenpolysiloxane having a SiH group compounded therewith are utilized in various uses.
- the curable silicone rubber compositions of this type are cured by the addition reaction (hydrosilylation reaction) between the SiH group of the crosslinking agent and the alkenyl group of the base polymer.
- Japanese Patent Pre-examination Publication (kokai) Nos. 62-47605, 62-49305, 62-47608, 4-243884, and 6-159510 describe a fluorine-containing organohydrogenpolysiloxane represented by the following general formula: wherein Rf is a divalent perfluoroalkylene group or a divalent perfluoropolyether group, and Me stands for a methyl group, or a fluorine-containing organohydrogenpolysiloxane represented by the following general formula: wherein Rf' is a monovalent perfluoroalkyl group or a monovalent perfluoropolyether group, and Me has the same meaning as above.
- an object of the present invention is to provide an organosilicon compound which has an improved compatibility with a fluorosilicone or fluoropolymer having a high fluorine-content and is useful as a crosslinking agent for addition-reaction curable silicone rubber compositions or addition-reaction curable fluororubber compositions each high in fluorine content, and a method for preparing the organosilicon compound.
- This invention provides an organosilicon compound represented by the following general formula (1): wherein R1 are independently a hydrogen atom or an unsubstituted or substituted monovalent hydrocarbon group, R are independently an alkylene group, Rf is a perfluoroalkylene group or a divalent perfluoropolyether group, and Z is a group having the general formula: wherein R3 are independently an unsubstituted or substituted monovalent hydrocarbon group, and a is an integer of 2 to 4.
- This invention provides also a method for preparing the organosilicon compound represented by said general formula (1), comprising subjecting an excess amount of a cyclic organohydrogenpolysiloxane represented by the following general formula (2): wherein R3 and a are as defined above, and a fluorine-containing amide compound having an unsaturated group represented by the following general formula (3): wherein Rf and R1 are as defined above, b are independently an integer of 0 to 4, and preferably 0 or 1, to partial addition reaction in the presence of a catalyst.
- the organosilicon compound of the present invention is useful as a crosslinking agent for addition-reaction curable silicone compositions. Particularly, this compound is useful as a crosslinking agent for addition-reaction curable fluorosilicone compositions and addition-reaction curable fluororubber compositions each high in fluorine content.
- Fig. 1 is an IR chart of the organosilicon compound of the present invention obtained in Example 1.
- Fig. 2 is an IR chart of the organosilicon compound of the present invention obtained in Example 2.
- Fig. 3 is an IR chart of the organosilicon compound of the present invention obtained in Example 3.
- the organosilicon compound of the present invention is represented by the above general formula (1).
- the unsubstituted or substituted monovalent hydrocarbon group of R1 is exemplified by an unsubstituted or substituted monovalent hydrocarbon group having 1 to 12 carbon atoms, for example, alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, neopentyl, hexyl, heptyl, octyl, nonyl, decyl, and dodecyl groups; cycloalkyl groups such as cyclopentyl, cyclohexyl, and cycloheptyl groups; alkenyl groups such as vinyl, ailyl, propenyl, isopropenyl, butenyl, isobutenyl, hexenyl, and cyclohexenyl
- the divalent alkylene group of R includes, for example, an alkylene group having 1 to 6 carbon atoms, such as methylene, ethylene, propylene, tetramethylene, hexamethylene, and methylpropylene, and preferably a straight chain or branched alkylene group having 2 to 4 carbon atoms, and more preferably ethylene and propylene groups.
- the perfluoroalkylene group of Rf includes, for example, a perfluoroalkylene group having 2 to 10 carbon atoms, such as -C2F4-, -C3F6-, -C4F8-, -C6F12- and -C8F16-, and preferably a straight chain perfluoroalkylene group having 2 to 8 carbon atoms, and more preferably -C4F8- and -C6F12-.
- the divalent perfluoropolyether group of Rf includes, for example, a straight chain or branched divalent perfluoropolyether group having 6 to 600 carbon atoms in which one or more repeating units such as -CF2O-, -CF2CF2O-, -CF2CF2CF2O- and -CF(CF3)OCF2- are contained, such as a perfluoropolyether group represented by the following formula: wherein m and n are each an integer so that m + n is 2 to 200, preferably 3 to 60, and more preferably 4 to 40; a perfluoropolyether group represented by the following formula: -CF20-(CF2CF20) p -(CF20) q -CF2- wherein p is an integer of 5 to 100, and q is an integer of 1 to 30; and a perfluoropolyether group represented by the following formula: -CF2CF20-(CF2CF2CF20) r
- the a in the above group Z is an integer of 2, 3 or 4.
- the compound of the present invention can be synthesized, for example, by subjecting an excess amount of a cyclic organohydrogenpolysiloxane represented by the following general formula (2): wherein R3 and a are as defined above, and a fluorine-containing amide compound having an unsaturated group represented by the following general formula (3): wherein Rf and R1 are as defined above, b are independently an integer of 0 to 4, and preferably 0 or 1, to partial addition reaction in the presence of a catalyst.
- the above catalyst includes, for example, the Group VIII elements of the periodic table and their compounds, such as, chloroplatinic acid; an alcohol-modified chloroplatinic acid (see U.S. Patent No. 3,220,972); a complex of chloroplatinic acid with an olefin (see U.S. Patent Nos. 3,159,601; 3,159,662; and 3,775,452); a platinum black, palladium or the like supported on a carrier such as alumina, silica or carbon; a rhodium-olefin complex; and chlorotris(triphenylphosphine)rhodium [Wilkinson's catalyst].
- chloroplatinic acid an alcohol-modified chloroplatinic acid
- a complex of chloroplatinic acid with an olefin see U.S. Patent Nos. 3,159,601; 3,159,662; and 3,775,452
- These complexes are preferably dissolved in an organic solvent such as alcohols, ketones or ethers for use.
- the reaction temperature is preferably 50 to 150 °C, and more preferably 60 to 120 °C.
- the amount of said catalyst used may be a so-called catalytic amount, for example, 1 to 1,000 ppm, preferably 10 to 500 ppm, in terms of a platinum family metal, based on the cyclic organohydrogenpolysiloxane.
- organosilicon compound is useful as a crosslinking agent for addition-reaction curable silicone rubber compositions.
- the addition-reaction curable silicone rubber compositions in which the organosilicon compound of the present invention is present as a crosslinking agent can be obtained, for example, by mixing an organopolysiloxane base polymer having an alkenyl group with the organosilicon compound in such an amount that the content of the SiH groups in said compound is 0.5 to 5 mol, preferably 0.8 to 3 mol, per mol of said alkenyl group and further mixing therewith a curing catalyst, a filler, and the like.
- the obtained addition-reaction curable silicone rubber compositions can be used for various uses, and particularly, a cured product obtained by curing a composition comprising an organopolysiloxane base polymer into which a fluorine-containing group has been introduced is excellent in adhesion to substrates.
- z is a group represented by the following formula: wherein Me stands for a methyl group, Ar stands for a group represented by the following formula: and m and n are each an integer of 5 to 27, provided that m + n equals to 32 on average.
Abstract
wherein R¹ are independently a hydrogen atom or an unsubstituted or substituted monovalent hydrocarbon group such as methyl, phenyl, 3,3,3-trifluoropropyl and 6,6,6,5,5,4,4,3,3-nonafluorohexyl groups, R are independently an alkylene group such as ethylene and propylene groups, Rf is a perfluoroalkylene group, such as -C₄F₈- and -C₆F₁₂-, or a divalent perfluoropolyether group, such as a group having the formula:
wherein m and n are each an integer such that m + n is 2 to 200, and Z is a group having the general formula:
wherein R³ are independently the same unsubstituted or substituted monovalent hydrocarbon group as the group R¹, and a is an integer of 2 to 4. This compound is useful as a crosslinking agent which is used when curing an unsaturated group-containing polymer by hydrosilylation reaction.
Description
- The present invention relates to an organosilicon compound useful as a crosslinking agent for addition-reaction curable silicone rubber compositions for use in various uses, and to a method for preparing the organosilicon compound.
- Conventionally, an addition-reaction curable silicone rubber composition comprising an organopolysiloxane having, as a base polymer, an alkenyl group such as vinyl group and, as a crosslinking agent, an organohydrogenpolysiloxane having a SiH group compounded therewith are utilized in various uses. The curable silicone rubber compositions of this type are cured by the addition reaction (hydrosilylation reaction) between the SiH group of the crosslinking agent and the alkenyl group of the base polymer.
- However, in the case of using, as a base polymer, a fluorosilicone or fluoropolymer high in fluorine content, even if a conventional organohydrogenpolysiloxane is used as a crosslinking agent, a good cured product could not be obtained from a silicone rubber composition comprised of a combination of said components since the crosslinking agent is poor in compatibility with the fluorosilicone or fluoropolymer high in fluorine content.
- Also, Japanese Patent Pre-examination Publication (kokai) Nos. 62-47605, 62-49305, 62-47608, 4-243884, and 6-159510 describe a fluorine-containing organohydrogenpolysiloxane represented by the following general formula:
- However, there has not hitherto been reported a compound in which two cyclic organohydrogensiloxanes are linked to each other through a divalent perfluoroalkylene group or a divalent perfluoropolyether group.
- Accordingly, an object of the present invention is to provide an organosilicon compound which has an improved compatibility with a fluorosilicone or fluoropolymer having a high fluorine-content and is useful as a crosslinking agent for addition-reaction curable silicone rubber compositions or addition-reaction curable fluororubber compositions each high in fluorine content, and a method for preparing the organosilicon compound.
- This invention provides an organosilicon compound represented by the following general formula (1):
- This invention provides also a method for preparing the organosilicon compound represented by said general formula (1), comprising subjecting an excess amount of a cyclic organohydrogenpolysiloxane represented by the following general formula (2):
- The organosilicon compound of the present invention is useful as a crosslinking agent for addition-reaction curable silicone compositions. Particularly, this compound is useful as a crosslinking agent for addition-reaction curable fluorosilicone compositions and addition-reaction curable fluororubber compositions each high in fluorine content.
- Fig. 1 is an IR chart of the organosilicon compound of the present invention obtained in Example 1.
- Fig. 2 is an IR chart of the organosilicon compound of the present invention obtained in Example 2.
- Fig. 3 is an IR chart of the organosilicon compound of the present invention obtained in Example 3.
- The present invention is hereinafter described in more detail.
- The organosilicon compound of the present invention is represented by the above general formula (1). In this formula, the unsubstituted or substituted monovalent hydrocarbon group of R¹ is exemplified by an unsubstituted or substituted monovalent hydrocarbon group having 1 to 12 carbon atoms, for example, alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, neopentyl, hexyl, heptyl, octyl, nonyl, decyl, and dodecyl groups; cycloalkyl groups such as cyclopentyl, cyclohexyl, and cycloheptyl groups; alkenyl groups such as vinyl, ailyl, propenyl, isopropenyl, butenyl, isobutenyl, hexenyl, and cyclohexenyl groups; aryl groups such as phenyl, tolyl, xylyl, naphthyl, and biphenyl groups; aralkyl groups such as benzyl, phenylethyl, phenylpropyl, and methylbenzyl groups; and groups derived from said exemplified groups by substituting at least part of the hydrogens bonded to the carbon atoms thereof with, for example, halogen atoms such as fluorine, chlorine and bromine, or cyano groups, such as chloromethyl, 2-bromoethyl, 3-chloropropyl, 3,3,3-trifluoropropyl, chlorophenyl, fluorophenyl, cyanoethyl, and 6,6,6,5,5,4,4,3,3-nonafluorohexyl groups, and preferably an unsubstituted or substituted monovalent hydrocarbon group free of aliphatic unsaturation having 1 to 8 carbon atoms, and more preferably methyl, phenyl, 3,3,3-trifluoropropyl, and 6,6,6,5,5,4,4,3,3-nonafluorohexyl groups.
- In the above general formula (1), the divalent alkylene group of R includes, for example, an alkylene group having 1 to 6 carbon atoms, such as methylene, ethylene, propylene, tetramethylene, hexamethylene, and methylpropylene, and preferably a straight chain or branched alkylene group having 2 to 4 carbon atoms, and more preferably ethylene and propylene groups.
- In the above general formula (1), the perfluoroalkylene group of Rf includes, for example, a perfluoroalkylene group having 2 to 10 carbon atoms, such as -C₂F₄-, -C₃F₆-, -C₄F₈-, -C₆F₁₂- and -C₈F₁₆-, and preferably a straight chain perfluoroalkylene group having 2 to 8 carbon atoms, and more preferably -C₄F₈- and -C₆F₁₂-.
- In the above general formula (1), the divalent perfluoropolyether group of Rf includes, for example, a straight chain or branched divalent perfluoropolyether group having 6 to 600 carbon atoms in which one or more repeating units such as -CF₂O-, -CF₂CF₂O-, -CF₂CF₂CF₂O- and -CF(CF₃)OCF₂- are contained, such as a perfluoropolyether group represented by the following formula:
-CF₂0-(CF₂CF₂0)p-(CF₂0)q-CF₂-
wherein p is an integer of 5 to 100, and q is an integer of 1 to 30; and a perfluoropolyether group represented by the following formula:
-CF₂CF₂0-(CF₂CF₂CF₂0)r-CF₂CF₂-
wherein r is an integer of 4 to 100; and preferably a straight chain or branched divalent perfluoropolyether group having 9 to 200 carbon atoms, and more preferably said perfluoropolyether group represented by the formula: - In the above general formula (1), the unsubstituted or substituted monovalent hydrocarbon group of R³ in the group Z represented by the following formula:
- The compound of the present invention can be synthesized, for example, by subjecting an excess amount of a cyclic organohydrogenpolysiloxane represented by the following general formula (2):
- The above catalyst includes, for example, the Group VIII elements of the periodic table and their compounds, such as, chloroplatinic acid; an alcohol-modified chloroplatinic acid (see U.S. Patent No. 3,220,972); a complex of chloroplatinic acid with an olefin (see U.S. Patent Nos. 3,159,601; 3,159,662; and 3,775,452); a platinum black, palladium or the like supported on a carrier such as alumina, silica or carbon; a rhodium-olefin complex; and chlorotris(triphenylphosphine)rhodium [Wilkinson's catalyst].
- These complexes are preferably dissolved in an organic solvent such as alcohols, ketones or ethers for use.
- The reaction temperature is preferably 50 to 150 °C, and more preferably 60 to 120 °C.
- The amount of said catalyst used may be a so-called catalytic amount, for example, 1 to 1,000 ppm, preferably 10 to 500 ppm, in terms of a platinum family metal, based on the cyclic organohydrogenpolysiloxane.
- The thus obtained organosilicon compound is useful as a crosslinking agent for addition-reaction curable silicone rubber compositions.
- The addition-reaction curable silicone rubber compositions in which the organosilicon compound of the present invention is present as a crosslinking agent can be obtained, for example, by mixing an organopolysiloxane base polymer having an alkenyl group with the organosilicon compound in such an amount that the content of the SiH groups in said compound is 0.5 to 5 mol, preferably 0.8 to 3 mol, per mol of said alkenyl group and further mixing therewith a curing catalyst, a filler, and the like. The obtained addition-reaction curable silicone rubber compositions can be used for various uses, and particularly, a cured product obtained by curing a composition comprising an organopolysiloxane base polymer into which a fluorine-containing group has been introduced is excellent in adhesion to substrates.
- The present invention will be hereinafter described in more detail.
- Into a four-necked 1-liter flask equipped with a stirrer, a thermometer, a reflux condenser and a dropping funnel, 152.1 g of 1,3,5,7-tetramethylcyclotetrasiloxane, 0.5 g of a toluene solution in which a complex of chloroplatinic acid with 1,3-divinyl-1,1,3,3-tetramethyldisiloxane has been dissolved in an amount of 0.5 weight % in terms of platinum atom, and 150 g of metaxylene hexafluoride were charged and heated to 80 °C. Then, into this flask, a solution prepared by dissolving, in 150 g of metaxylene hexafluoride, 140.8 g of a fluorine-containing allylamide represented by the following structural formula:
-
- δ 0.01 ppm is, Si-CH₃, 24H)
- δ 0.41 ppm (m, Si-CH₂, 4H)
- δ 1.53 ppm (m, C-CR₂-C, 4H)
- δ 3.52 ppm (t, N-CH₂, 4H)
- δ 4.49 ppm ( s , Si-H, 6H)
- δ 6.8-7.3 ppm (m, arom., 10H)
-
- νSi-H : 2170 cm⁻¹
- νC=O : 1695 cm⁻¹
-
C H O Si Found 24.06 % 0.86 % 11.03 % 3.69 % Calc'd 24.18 % 0.79 % 11.10 % 3.72 % - Into a four-necked 1-liter flask equipped with a stirrer, a thermometer, a reflux condenser and a dropping funnel, 125.1 g of 1,3,5,7,9-pentamethylcyclopentasiloxane, 0.1 g of a toluene solution in which a complex of chloroplatinic acid with 1,3-divinyl-1,1,3,3-tetramethyldisiloxane has been dissolved in an amount of 0.5 weight % in terms of platinum atom, and 120 g of metaxylene hexafluoride were charged and heated to 80 °C. Then, into this flask, a solution prepared by dissolving, in 20 g of metaxylene hexafluoride, 20.0 g of a fluorine-containing allylamide represented by the following structural formula:
-
- δ 0.04 ppm (s, Si-CH₃, 30H)
- δ 0.47 ppm (m, Si-CH₂, 4H)
- δ 1.51 ppm (m, C-CH₂-C, 4H)
- δ 3.17 ppm (t, N-CH₂, 4H)
- δ 4.53 ppm (s, Si-H, 8H)
- δ 6.74 ppm (s, N-H, 2H)
-
- νN-H : 3330 cm⁻¹
- νSi-H : 2170 cm⁻¹
- νC=O : 1700 cm⁻¹
-
C H O Si Found 29.47 % 4.94 % 16.25 % 22.88 % Calc'd 29.50 % 4.95 % 16.37 % 22.99 % - Into a four-necked 1-liter flask equipped with a stirrer, a thermometer, a reflux condenser and a dropping funnel, 28.0 g of 1,3,5,7-tetramethylcyclotetrasiloxane, 0.05 g of a toluene solution in which a complex of chloroplatinic acid with 1,3-divinyl-1,1,3,3-tetramethyldisiloxane has been dissolved in an amount of 0.5 weight % in terms of platinum atom, and 20 g of metaxylene hexafluoride were charged and heated to 80 °C. Then, into this flask, a solution prepared by dissolving, in 20 g of metaxylene hexafluoride, 20.0 g of a fluorine-contaning allylamide represented by the following structural formula:
-
- δ 0.01 ppm (s, Si-CH₃, 24H)
- δ 0.41 ppm (m, Si-CH₂, 4H)
- δ 1.54 ppm (m, C-CH₂-C, 4H)
- δ 3.54 ppm (t, N-CH₂, 4H)
- δ 4.41 ppm (s, Si-H, 6H)
- δ 7.1-7.6 ppm (m, arom., 8H)
-
- νSi-H : 2170 cm⁻¹
- νC=O : 1700 cm⁻¹
-
C H O Si Found 24.25 % 0.79 % 10.70 % 3.62 % Calc'd 24.21 % 0.81 % 10.75 % 3.59 %
Claims (10)
- An organosilicon compound represented by the following general formula (1):
- The organosilicon compound according to claim 1, wherein the R¹ in said general formula (1) are an unsubstituted or substituted monovalent hydrocarbon group free of aliphatic unsaturation having 1 to 12 carbon atoms.
- The organosilicon compound according to claim 1, wherein the R¹ in said general formula (1) are selected from the group consisting of methyl, phenyl, 3,3,3-trifluoropropyl, and 6,6,6,5,5,4,4,3,3-nonafluorohexyl groups.
- The organosilicon compound according to claim 1, wherein the R in said general formula (1) are a straight chain or branched alkylene group having 1 to 6 carbon atoms.
- The organosilicon compound according to claim 1, wherein the R in said general formula (I) are selected from the group consisting of ethylene and propylene groups.
- The organosilicon compound according to claim 1, wherein the perfluoroalkylene group among the Rf in said general formula (1) is a straight chain perfluoroalkylene group having 2 to 10 carbon atoms, and the divalent perfluoropolyether group among the Rf in said general formula (1) is a straight chain or branched divalent perfluoropolyether group having 6 to 600 carbon atoms in which one or more repeating units selected from the group consisting of -CF₂O-, -CF₂CF₂O-, -CF₂CF₂CF₂O-, and -CF(CF₃)OCF₂- are contained.
- The organosilicon compound according to claim 1, wherein the perfluoroalkylene group among the Rf in said general formula (1) are selected from the group consisting of -C₂F₄-, -C₃F₆-, -C₄F₈-, -C₄F₁₂- and -C₈F₁₆-, and the divalent perfluoropolyether group among the Rf in said general formula (1) is a group represented by the formula:
- The organosilicon compound according to claim 1, wherein the R³ in the group Z of said general formula (1) are an unsubstituted or substituted monovalent hydrocarbon group free of aliphatic unsaturation having 1 to 12 carbon atoms.
- The organosilicon compound according to claim 1, wherein the R³ in the group Z of said general formula (1) are selected from the group consisting of methyl, phenyl, 3,3,3-trifluoropropyl, and 6,6,6,5,5,4,4,3,3-nonafluorohexyl groups.
- A method for preparing the organosilicon compound of claim 1, which comprises subjecting an excess amount of a cyclic organohydrogenpolysiloxane represented by the following general formula (2):
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP30299894 | 1994-11-11 | ||
JP302998/94 | 1994-11-11 | ||
JP6302998A JP2963022B2 (en) | 1994-11-11 | 1994-11-11 | Organic silicon compounds |
Publications (2)
Publication Number | Publication Date |
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EP0711781A1 true EP0711781A1 (en) | 1996-05-15 |
EP0711781B1 EP0711781B1 (en) | 2000-02-02 |
Family
ID=17915711
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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EP95308053A Expired - Lifetime EP0711781B1 (en) | 1994-11-11 | 1995-11-10 | Organosilicon compound and a method for preparing the same |
Country Status (4)
Country | Link |
---|---|
US (1) | US5554779A (en) |
EP (1) | EP0711781B1 (en) |
JP (1) | JP2963022B2 (en) |
DE (1) | DE69514888T2 (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
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US6451396B1 (en) | 1998-02-13 | 2002-09-17 | Gore Enterprise Holdings, Inc. | Flexure endurant composite elastomer compositions |
JP3594113B2 (en) * | 1998-07-16 | 2004-11-24 | 信越化学工業株式会社 | Fluorine-containing amide compound |
US7642332B2 (en) * | 2006-08-14 | 2010-01-05 | The University Of Akron | Amphiphilic networks, process for producing same, and products made therefrom |
Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3159601A (en) | 1962-07-02 | 1964-12-01 | Gen Electric | Platinum-olefin complex catalyzed addition of hydrogen- and alkenyl-substituted siloxanes |
US3159662A (en) | 1962-07-02 | 1964-12-01 | Gen Electric | Addition reaction |
US3220972A (en) | 1962-07-02 | 1965-11-30 | Gen Electric | Organosilicon process using a chloroplatinic acid reaction product as the catalyst |
US3775452A (en) | 1971-04-28 | 1973-11-27 | Gen Electric | Platinum complexes of unsaturated siloxanes and platinum containing organopolysiloxanes |
JPS6247608A (en) | 1985-08-28 | 1987-03-02 | Asahi Glass Co Ltd | Optical transmission fiber using plastic clad |
JPS6247605A (en) | 1985-08-28 | 1987-03-02 | Asahi Glass Co Ltd | Clad material for optical transmission fiber |
JPS6249305A (en) | 1985-08-28 | 1987-03-04 | Asahi Glass Co Ltd | Clad material composition for optical transmission fiber |
EP0496597A1 (en) * | 1991-01-24 | 1992-07-29 | Shin-Etsu Chemical Co., Ltd. | Preparation of hydrogensiloxanes |
EP0573282A1 (en) * | 1992-06-02 | 1993-12-08 | Shin-Etsu Chemical Co., Ltd. | Fluorine-containing organosilicon compounds |
JPH06159510A (en) | 1992-11-20 | 1994-06-07 | Hitachi Metals Ltd | Pressure tank |
EP0601883A2 (en) * | 1992-12-10 | 1994-06-15 | Shin-Etsu Chemical Co., Ltd. | Adhesive silicone rubber compositions, their preparation and use |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0573283B1 (en) * | 1992-06-02 | 1997-10-08 | Shin-Etsu Chemical Co., Ltd. | Fluorine-containing organopolysiloxane composition |
-
1994
- 1994-11-11 JP JP6302998A patent/JP2963022B2/en not_active Expired - Fee Related
-
1995
- 1995-11-10 EP EP95308053A patent/EP0711781B1/en not_active Expired - Lifetime
- 1995-11-10 DE DE69514888T patent/DE69514888T2/en not_active Expired - Fee Related
- 1995-11-13 US US08/558,001 patent/US5554779A/en not_active Expired - Lifetime
Patent Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3159601A (en) | 1962-07-02 | 1964-12-01 | Gen Electric | Platinum-olefin complex catalyzed addition of hydrogen- and alkenyl-substituted siloxanes |
US3159662A (en) | 1962-07-02 | 1964-12-01 | Gen Electric | Addition reaction |
US3220972A (en) | 1962-07-02 | 1965-11-30 | Gen Electric | Organosilicon process using a chloroplatinic acid reaction product as the catalyst |
US3775452A (en) | 1971-04-28 | 1973-11-27 | Gen Electric | Platinum complexes of unsaturated siloxanes and platinum containing organopolysiloxanes |
JPS6247608A (en) | 1985-08-28 | 1987-03-02 | Asahi Glass Co Ltd | Optical transmission fiber using plastic clad |
JPS6247605A (en) | 1985-08-28 | 1987-03-02 | Asahi Glass Co Ltd | Clad material for optical transmission fiber |
JPS6249305A (en) | 1985-08-28 | 1987-03-04 | Asahi Glass Co Ltd | Clad material composition for optical transmission fiber |
EP0496597A1 (en) * | 1991-01-24 | 1992-07-29 | Shin-Etsu Chemical Co., Ltd. | Preparation of hydrogensiloxanes |
JPH04243884A (en) | 1991-01-24 | 1992-08-31 | Shin Etsu Chem Co Ltd | Production of hydrogensiloxane |
EP0573282A1 (en) * | 1992-06-02 | 1993-12-08 | Shin-Etsu Chemical Co., Ltd. | Fluorine-containing organosilicon compounds |
JPH06159510A (en) | 1992-11-20 | 1994-06-07 | Hitachi Metals Ltd | Pressure tank |
EP0601883A2 (en) * | 1992-12-10 | 1994-06-15 | Shin-Etsu Chemical Co., Ltd. | Adhesive silicone rubber compositions, their preparation and use |
Also Published As
Publication number | Publication date |
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JPH08134084A (en) | 1996-05-28 |
EP0711781B1 (en) | 2000-02-02 |
DE69514888T2 (en) | 2000-10-05 |
US5554779A (en) | 1996-09-10 |
DE69514888D1 (en) | 2000-03-09 |
JP2963022B2 (en) | 1999-10-12 |
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